On the Street Where You Live (Vic Damone)
Memorably employed in the very first episode of Mad Men, this song from the Broadway musical My Fair Lady was a top-10 hit for Vic Damone in 1958. The song tells the story of a man bewitched and bewildered by this crazy thing called love and Damone fittingly varies the lyrics between a near whisper and operatic roar. When he raises the key in the closing coda, goosebumps emerge.

The Way You Look Tonight (Frank Sinatra)
An Oscar-winner for Best Original Song in 1936 (as performed by Fred Astaire in the movie Swing Time), this heartfelt ode to true love was a perfect fit for Old Blue Eyes. Sinatra recorded the song in 1964, following two failed marriages and countless romantic dalliances, and he pours his heart into the lyrics by Jerome Kern and Dorothy Fields. If you truly love someone, you will have slow-danced with them to this song at least once.

Wicked Game (Chris Isaak)
The apex of Chris Isaak’s musical career was this smoldering 1989 hit that still receives marathon airplay each Valentine’s Day. The simple lyrics tell of a man smitten by a temptress (“What a wicked game you played/To make me feel this way”), performed with mournful intensity by Isaak. No question the song’s success was aided immeasurably by fashion photographer Herb Ritts’ sexy black-and-white music video, which consisted largely of half-naked model Helena Christensen rolling around on the beach. Hubba-hubba.

My Heart Will Go On (Celine Dion)
Alternately known as “The Titanic Theme,” this 1997 was the biggest hit of Celine Dion’s career–more than 15-million copies sold worldwide. The aching love ballad was written expressly for James Cameron’s epic movie about the ill-fated ship and the great Canadian chanteuse completely sells the hopeful, if slightly corny, lyrics (“Near, far, where-ever you are”) that served as backdrop to the star-crossed onscreen love between Leonardo DiCaprio and Kate Winslet. And you just know Celine closes every one of her shows in Vegas with this song.

(Everything I Do) I Do It For You (Bryan Adams)
If Bryan Adams received a dollar for every time this song was played as the first-dance song at weddings, he could probably buy his hometown of Kingston, Ontario. The song was the standout entry on the 1991 film Robin Hood: Prince of Thieves and still ranks among the biggest hits of Adams’ career. The lyrics elevate the song a notch about your standard power ballad, with Adams’ scratch voice well-suited to the yearning prose (“I would fight for you/I’d lie for you/Walk the wire for you/Yeah, I’d die for you”). What’s the song’s connection to Kevin Costner’s portrayal of Robin Hood? Thankfully, nothing.

I Love the Way You Lie (Eminem with Rihanna)
The old adage about the course of true love never running smoothly is evinced perfectly in this 2010 chart-topper. Rapper Eminem and Rihanna (who surely knows a thing or two about broken romance) engage in a no-holds-barred vocal brawl. Him: “You ever love somebody so much you can barely breathe when you’re with ‘em?” Her: “Just gonna stand there and watch me burn/That’s alright because I like the way it hurts.” A soundtrack to true love gone wrong.

Grenade (Bruno Mars)
Still the preferred audition song of nearly half of American Idol contestants, this 2010 single by elfin pop star Bruno Mars provides a lilting snapshot of selfless love. Mars bares his soul for all the world to hear and it’s more than apparent that the object of his affection isn’t responding in kind. Listen to it again and ask yourself: Would you catch a grenade for that special person in your life?